Sodium Carbonate → HCID 135738577, compound

HRID 862908Notes

Reaction equation

HRID 862908 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:11][C:12](=[O:23])[C:13]2[N:18]([CH3:19])[N:17]=[C:16]([CH2:20][O:21][CH3:22])[C:14]=2[N:15]=1)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[CH3:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1.Cl[S:38](O)(=[O:40])=[O:39]>>[CH3:22][O:21][CH2:20][C:16]1[C:14]2[N:15]=[C:10]([C:5]3[CH:6]=[C:7]([S:38]([N:34]4[CH2:35][CH2:36][N:31]([CH3:30])[CH2:32][CH2:33]4)(=[O:40])=[O:39])[CH:8]=[CH:9][C:4]=3[O:3][CH2:1][CH3:2])[NH:11][C:12](=[O:23])[C:13]=2[N:18]([CH3:19])[N:17]=1

Participants

5

Reactant 4

HCID 10340Sodium CarbonateHCID 24638Chlorosulfonic acidHCID 531671-MethylpiperazineHCID 135738564HCID 135738564, compound

Product 1

HCID 135738577HCID 135738577, compoundYield 7%

Procedure

5-(2-Ethoxyphenyl)-3-methoxymethyl-1-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (470 mg, 1.50 mmol) was dissolved in chlorosulphonic acid (3 ml) at 0° C. The solution was stirred at room temperature for 2 hours, then cautiously added to ice-water (50ml). The resulting solution was neutralised with saturated sodium carbonate solution, then extracted with a 20:1 mixture of dichloromethane and methanol (2×50 ml). The combined organic extracts were evaporated under vacuum and the residue was dissolved in ethanol (5 ml) and the solution treated with N-methylpiperazine (450 mg, 4.5 mmol). After 1 hour at room temperature the solvent was evaporated under vacuum and the residue chromotographed on silica gel, eluting with a mixture of dichlormethane, methanol and aqueous ammonium hydroxide solution (90:10:1 by volume). Trituration of the crude product with ethyl acetate gave the title compound as a white solid (49 mg, 7%), m.p. 198°-199° C. Found: C,52.94; H,6.04; N,17.67. C21H28N6O5S requires C,52.93; H, 5.92; N,17.64%.

Workup

  1. extractionextracted with a 20:1 mixture of dichloromethane and methanol (2×50 ml)
  2. customThe combined organic extracts were evaporated under vacuum
  3. dissolutionthe residue was dissolved in ethanol (5 ml)
  4. customAfter 1 hour at room temperature the solvent was evaporated under vacuum
  5. washthe residue chromotographed on silica gel, eluting with a mixture of dichlormethane, methanol and aqueous ammonium hydroxide solution (90:10:1 by volume)

Sources & evidence

ORD record
ord-54756d7a0ff944539a4067af1cbbb79f
Source dataset
uspto-grants-1998_02
Patent number
US05719283

Reaction notes

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